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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 720144Generated: October 29, 2026

Methanol → (2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/720144

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantDimethylformamideHCID 6228—
Reactant(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterHCID 136141708—
CatalystPalladiumHCID 23938—
SolventEthyl AcetateHCID 8857—
Product(2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterHCID 13598471469%

Reaction Steps

Palladium (10% on activated carbon) (0.23 g, 0.198 mmol) was added to a solution of the title compound of Example 164 (0.65 g, 1.99 mmol) in 1:10 N,N-dimethylformamide:methanol (11 mL). The reaction mixture was purged with H2 and stirred at room temperature under H2 (1 atm.) for 5 hours. The palladium was filtered and the volatile components were removed in vacuo. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 1.2:1 dichloromethane:ethyl acetate to afford the title compound (0.45 g, 1.37 mmol) as a yellow solid in 69% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07132533B2
Source datasetuspto-grants-2006_11
ORD IDord-5e752a020bbb4e4d92fc234806e362df
Source noteuspto-grants-2006_11